Acetic Anhydride → HCID 57703495, compound

HRID 2382510Notes

Reaction equation

HRID 2382510 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[CH:17]=O.CC(OC(C)=O)=O.C(N(CC)CC)C>CCCCCC.C(OCC)(=O)C>[CH3:23][O:22][C:20]1[CH:19]=[C:16](/[CH:17]=[C:8](/[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)\[C:9]([OH:11])=[O:10])[CH:15]=[C:14]([O:13][CH3:12])[CH:21]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 98372-(4-Fluorophenyl)acetic acidHCID 817473,5-Dimethoxybenzaldehyde

Product 1

HCID 57703495HCID 57703495, compoundYield 82.87%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluorophenyl acetic acid (0.928 g, 6.02 mmol), 3,5 dimethoxybenzaldehyde (1 g, 6.02 mmole), Ac2O (1 ml) and triethylamine (0.5 ml) was heated at 100° C. for 12 hours. Upon completion (as monitored by TLC using hexane-ethyl acetate (3:2), the reaction mixture was cooled to room temperature and concentrated HCL (5 ml) was added. The precipitate was dissolved in CH2Cl2 (100 ml), washed with 10% aqueous NaOH (3×50 ml) and the basic solution was acidified (PH-1) with concentrated HCL. After stirring, the precipitate was collected and dried to get the product (1.5 g, 82.87%).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationconcentrated HCL (5 ml)
  3. additionwas added
  4. dissolutionThe precipitate was dissolved in CH2Cl2 (100 ml)
  5. washwashed with 10% aqueous NaOH (3×50 ml)
  6. customthe precipitate was collected
  7. customdried

Sources & evidence

ORD record
ord-a780e0ca3e2f4a808a1d63bc87d7ddc9
Source dataset
uspto-grants-2012_09
Patent number
US08263044B2

Reaction notes

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